Real Estate Investment Properties for Sale in Oakland, MO

Looking for investment property in Oakland, MO with high ROI ?

Explore a variety of short-term homes & houses in Oakland, MO. Invest wisely with VRBO & Oakland, MO Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Oakland, MO

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
The Birch Plan Oakland, MO The Birch Plan, Oakland, MO 53122 \| Townhouse	3 beds \| 2 baths \| 2,000 sq.ft.	$600,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 1.47% Airbnb Rental Income: $1802 Traditional Rental Income: $2014 Airbnb ROI: 0.21% Traditional ROI: 1.47%
1187 Hawken Pl Oakland, MO	3 beds \| 2 baths \| 2,636 sq.ft.	$509,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 0.48% Airbnb Rental Income: $1802 Traditional Rental Income: $1913 Airbnb ROI: -0.78% Traditional ROI: 0.48%
48 Webster Woods Dr Oakland, MO 48 Webster Woods Dr, Oakland, MO 63119 \| Single Family Residential	4 beds \| 3 baths \| 2,499 sq.ft.	$750,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 1.37% Airbnb Rental Income: $1586 Traditional Rental Income: $2468 Airbnb ROI: -0.54% Traditional ROI: 1.37%
624 Locksley Pl Oakland, MO 624 Locksley Pl, Oakland, MO 63119 \| Single Family Residential	4 beds \| 3 baths \| 2,624 sq.ft.	$1,100,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 0.46% Airbnb Rental Income: $1586 Traditional Rental Income: $2574 Airbnb ROI: -0.95% Traditional ROI: 0.46%
550 Locust Ct Oakland, MO 550 Locust Ct, Oakland, MO 63119 \| Single Family Residential	3 beds \| 3 baths \| 1,701 sq.ft.	$595,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 1.25% Airbnb Rental Income: $1802 Traditional Rental Income: $1876 Airbnb ROI: 0.23% Traditional ROI: 1.25%
767 Windberry Ct #24 Oakland, MO Make yourself at home! This super cute condo in a super convenient location has it all: Op...	2 beds \| 2 baths \| 1,300 sq.ft.	$310,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 1.7% Airbnb Rental Income: $1454 Traditional Rental Income: $1384 Airbnb ROI: 0.47% Traditional ROI: 1.7%
110 N Holmes Ave Oakland, MO This charming brick beauty w/ adorable curb appeal is perfectly located in the heart of Hi...	3 beds \| 2 baths \| 1,875 sq.ft.	$499,900	Airbnb cash on cash: 0.74% Traditional cash on cash: 1.83% Airbnb Rental Income: $1802 Traditional Rental Income: $1824 Airbnb ROI: 0.74% Traditional ROI: 1.83%
326 Luther Ln Oakland, MO Desirable location in Glendale on a .57 acre lot! This home has a 10 Â½ ft coffered ceilin...	3 beds \| 2 baths \| 3,906 sq.ft.	$1,150,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 1.22% Airbnb Rental Income: $1802 Traditional Rental Income: $3288 Airbnb ROI: -0.63% Traditional ROI: 1.22%
401 Meacham St Oakland, MO 3 bed 1 bath in sought after Kirkwood ready for a new owner.	3 beds \| 1 baths \| 912 sq.ft.	$259,000	Airbnb cash on cash: 3.44% Traditional cash on cash: 2.72% Airbnb Rental Income: $1802 Traditional Rental Income: $1138 Airbnb ROI: 3.44% Traditional ROI: 2.72%
649 South Sappington Blvd Oakland, MO 649 South Sappington Blvd, Oakland, MO 63122 \| Other	N/A beds \| N/A baths \| N/A	$179,900	Airbnb cash on cash: 2.02% Traditional cash on cash: 1.81% Airbnb Rental Income: $1156 Traditional Rental Income: $738 Airbnb ROI: 2.02% Traditional ROI: 1.81%
645 S Elliott Tbb Ave Oakland, MO 645 S Elliott Tbb Ave, Oakland, MO 63122 \| Single Family Residential	4 beds \| 2 baths \| 2,372 sq.ft.	$849,900	Airbnb cash on cash: -0.65% Traditional cash on cash: 0.25% Airbnb Rental Income: $1586 Traditional Rental Income: $1847 Airbnb ROI: -0.65% Traditional ROI: 0.25%
9722 Big Bend Blvd Oakland, MO 9722 Big Bend Blvd, Oakland, MO 63122 \| Single Family Residential	4 beds \| 2 baths \| 2,194 sq.ft.	$419,900	Airbnb cash on cash: 0.68% Traditional cash on cash: 2.61% Airbnb Rental Income: $1586 Traditional Rental Income: $1893 Airbnb ROI: 0.68% Traditional ROI: 2.61%
7 A Melshire Ct Oakland, MO 7 A Melshire Ct, Oakland, MO 63122 \| Other	N/A beds \| N/A baths \| N/A	$375,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 0.06% Airbnb Rental Income: $1156 Traditional Rental Income: $803 Airbnb ROI: -0.03% Traditional ROI: 0.06%
721 Oakway Pl Oakland, MO 721 Oakway Pl, Oakland, MO 63122 \| Single Family Residential	3 beds \| 2 baths \| 1,628 sq.ft.	$475,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 1.16% Airbnb Rental Income: $1802 Traditional Rental Income: $1479 Airbnb ROI: 0.78% Traditional ROI: 1.16%
431 New York St Oakland, MO 431 New York St, Oakland, MO 63122 \| Single Family Residential	4 beds \| 2 baths \| 1,505 sq.ft.	$350,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 2.64% Airbnb Rental Income: $1586 Traditional Rental Income: $1607 Airbnb ROI: 1.2% Traditional ROI: 2.64%
738 Windberry Ct #9 Oakland, MO 738 Windberry Ct #9, Oakland, MO 63122 \| Single Family Residential	2 beds \| 2 baths \| 1,423 sq.ft.	$429,900	Airbnb cash on cash: -1.03% Traditional cash on cash: 0.52% Airbnb Rental Income: $1454 Traditional Rental Income: $1647 Airbnb ROI: -1.03% Traditional ROI: 0.52%
738 Windberry Ct #9 Oakland, MO 738 Windberry Ct #9, Oakland, MO 63122 \| Single Family Residential	2 beds \| 2 baths \| 1,423 sq.ft.	$429,900	Airbnb cash on cash: -1.03% Traditional cash on cash: 0.52% Airbnb Rental Income: $1454 Traditional Rental Income: $1647 Airbnb ROI: -1.03% Traditional ROI: 0.52%
738 Windberry Ct #9 Oakland, MO 738 Windberry Ct #9, Oakland, MO 63122 \| Single Family Residential	2 beds \| 2 baths \| 1,423 sq.ft.	$429,900	Airbnb cash on cash: -1.03% Traditional cash on cash: 0.52% Airbnb Rental Income: $1454 Traditional Rental Income: $1647 Airbnb ROI: -1.03% Traditional ROI: 0.52%
1027 LEAWOOD DR Oakland, MO Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 1 baths \| 944 sq.ft.	$243,000	Airbnb cash on cash: 3.57% Traditional cash on cash: 3.2% Airbnb Rental Income: $1802 Traditional Rental Income: $1229 Airbnb ROI: 3.57% Traditional ROI: 3.2%
829 S Sappington Rd Oakland, MO 829 S Sappington Rd, Oakland, MO 63126 \| Other	N/A beds \| N/A baths \| N/A	$150,000	Airbnb cash on cash: 2.79% Traditional cash on cash: 3.19% Airbnb Rental Income: $1156 Traditional Rental Income: $831 Airbnb ROI: 2.79% Traditional ROI: 3.19%
1018 Ferndale Ave Oakland, MO 1018 Ferndale Ave, Oakland, MO 63126 \| Single Family Residential	2 beds \| 1 baths \| 850 sq.ft.	$165,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 2.77% Airbnb Rental Income: $1454 Traditional Rental Income: $837 Airbnb ROI: 3.95% Traditional ROI: 2.77%

Real Estate investment in Oakland, MO

There are 20 properties for sale in the city of Oakland . The median list price in Oakland is $429,778 and the average price per square foot is $257. In June 2026, the average monthly cash on cash return in Oakland is 2.00%. The average monthly rental income in Oakland is $1,647.

Oakland, MO Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 20 investment properties available for sale in Oakland.

In 2026, the best neighborhood to buy investment property is Oakland.

The ROI for Long-Term is higher than the Short-Term in Oakland with average rental income of $1,647.

Your search for investment property begins and ends here

Investment Property for Sale in Oakland, MO

The Birch Plan

Oakland, MO

3 beds | 2 baths | 2,000 sq.ft.

$600,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: 1.47%

Airbnb Rental Income: $1802

Traditional Rental Income: $2014

Airbnb ROI: 0.21%

Traditional ROI: 1.47%

1187 Hawken Pl

Oakland, MO

3 beds | 2 baths | 2,636 sq.ft.

$509,000

Airbnb cash on cash: -0.78%

Traditional cash on cash: 0.48%

Airbnb Rental Income: $1802

Traditional Rental Income: $1913

Airbnb ROI: -0.78%

Traditional ROI: 0.48%

48 Webster Woods Dr

Oakland, MO

4 beds | 3 baths | 2,499 sq.ft.

$750,000

Airbnb cash on cash: -0.54%

Traditional cash on cash: 1.37%

Airbnb Rental Income: $1586

Traditional Rental Income: $2468

Airbnb ROI: -0.54%

Traditional ROI: 1.37%

624 Locksley Pl

Oakland, MO

4 beds | 3 baths | 2,624 sq.ft.

$1,100,000

Airbnb cash on cash: -0.95%

Traditional cash on cash: 0.46%

Airbnb Rental Income: $1586

Traditional Rental Income: $2574

Airbnb ROI: -0.95%

Traditional ROI: 0.46%

550 Locust Ct

Oakland, MO

3 beds | 3 baths | 1,701 sq.ft.

$595,000

Airbnb cash on cash: 0.23%

Traditional cash on cash: 1.25%

Airbnb Rental Income: $1802

Traditional Rental Income: $1876

Airbnb ROI: 0.23%

Traditional ROI: 1.25%

767 Windberry Ct #24

Oakland, MO

2 beds | 2 baths | 1,300 sq.ft.

$310,000

Airbnb cash on cash: 0.47%

Traditional cash on cash: 1.7%

Airbnb Rental Income: $1454

Traditional Rental Income: $1384

Airbnb ROI: 0.47%

Traditional ROI: 1.7%

110 N Holmes Ave

Oakland, MO

3 beds | 2 baths | 1,875 sq.ft.

$499,900

Airbnb cash on cash: 0.74%

Traditional cash on cash: 1.83%

Airbnb Rental Income: $1802

Traditional Rental Income: $1824

Airbnb ROI: 0.74%

Traditional ROI: 1.83%

326 Luther Ln

Oakland, MO

3 beds | 2 baths | 3,906 sq.ft.

$1,150,000

Airbnb cash on cash: -0.63%

Traditional cash on cash: 1.22%

Airbnb Rental Income: $1802

Traditional Rental Income: $3288

Airbnb ROI: -0.63%